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Pregled bibliografske jedinice broj: 871831

Zbornik radova

Autori: Škalamera, Đani; Blažek Bregović, Vesna; Basarić, Nikola
Naslov: New aniline photocage for carboxylic acids
Izvornik: 25. Hrvatski skup kemičara i kemijskih inženjera s međunarodnim sudjelovanjem 3. simpozij "Vladimir Prelog" / Poreč, Hrvatska
Skup: 25. HSKIKI
Mjesto i datum: Poreč, Hrvaska, 19-22.04.2017.
Ključne riječi: anilines, photocage, photochemistry, protective groups
Sažetak:
Photocleavable protecting groups (PPGs, photocages) are extensively used in chemical and biological sciences. It was shown that they can be used for light-controlled small molecule release (NO, H2S, CO, HNO) in biological systems [1], photocontrolled targeted drug delivery [2] and in molecular imaging and cell biology [3]. Very important area for application of PPGs is organic synthesis. Typical protecting groups used in organic synthesis (e.g. Boc, Fmoc) require some specific reagents/conditions for their removal. On the other hand, for removal of PPGs only iradiation is required (usually UV), which is big advantage in comparison with the standard protecting groups. Three main classes of PPGs described in the literature are based on: 2-nitrobenzyl, carbonyl or benzyl moieties.[4] However, these PPGs suffer from some limitations in their application, e. g. for 2-nitrobenzylalcohols the decaging reaction is slow. Therefore, research for new PPGs is very important topic of current research in organic photochemistry. Wang et al. have recently reported an interesting example of photocage for alcohols, based on m-hydroxyaniline ethers.[5] We decided to further develop this type of protecting group and expand their application for the protection of carboxylic acids. A systematic study of photochemical reactivity was conducted on o-, m- and p-substituted aniline-based PPGs. We have found out that a range of structurally different carboxylic acids can be easily converted to o-hydroxymehtylaniline esters ih high yield. The photodeprotection was accomplished under mild conditions (aqueous CH3CN), using 300 nm light. After the photodecageing, only aqueous workup (extraction) was required to obtain pure acid, without the need for the product chromatographic purification or crystallization. Furthermore, we have demonstrated that aniline alcohol can be regenerated from the photodeprotection reaction and reused.
Vrsta sudjelovanja: Poster
Vrsta prezentacije u zborniku: Sažetak
Vrsta recenzije: Međunarodna recenzija
Projekt / tema: fotokemija anilinskih derivata u svrhu razvoja novih fotouklonjivih zaštitnih skupina, Projekt HAZU - Sinteza, HRZZ-IP-2014-09-6312
Izvorni jezik: ENG
Kategorija: Znanstveni
Znanstvena područja:
Kemija
Upisao u CROSBI: Enidija Lukša (Enidija.Luksa@irb.hr), 24. Tra. 2017. u 10:52 sati
Napomene:
anilines, photocage, photochemistry, protective groups



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